2-Methyl-2-butene → HCID 86698770, compound

Participants

Reaction Conditions

Reaction Steps

1-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]cyclopropanecarboxylic acid (253 mg, 0.577 mmol) was dissolved in MeCN (6 mL) and warm t-butanol (6 mL). 2-methyl-2-butene (4 mL) was added and the mixture was cooled to 0° C. Sodium chlorite (780 mg, 11.6 mmol) and sodium dihydrogen phosphate dihydrate (1800 mg, 11.54 mmol) were dissolved in water (4 mL). The aqueous solution was added to the organic solution dropwise via addition funnel and the ice bath was removed and the mixture was allowed to warm to room temperature overnight. The reaction was concentrated to remove the organics and extracted with ethyl acetate (20 mL×3). The combined organics were washed with brine (20 mL), dried and concentrated and then purified by reverse phase HPLC to give the title compound (62.4 mg, 30.5% yield) as a white solid. MS (AP+) 377.9 (M+Na)+. 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.40 (m, 4H), 1.61 (m, 2H), 1.27 (m, 2H).

Provenance & Evidence